Latamoxef

Latamoxef
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Intramuscular, intravenous
ATC code
Pharmacokinetic data
Protein binding35 to 50%
MetabolismNil
Elimination half-life2 hours
ExcretionMostly renal, unchanged; also biliary
Identifiers
  • (6R,7R)-7-{[carboxy(4-hydroxyphenyl)acetyl]amino}-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.059.334 Edit this at Wikidata
Chemical and physical data
FormulaC20H20N6O9S
Molar mass520.47 g·mol−1
3D model (JSmol)
Melting point117 to 122 °C (243 to 252 °F) (dec.)
  • O=C2N1/C(=C(\CO[C@@H]1[C@]2(OC)NC(=O)C(c3ccc(O)cc3)C(=O)O)CSc4nnnn4C)C(=O)O
  • InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1 checkY
  • Key:JWCSIUVGFCSJCK-CAVRMKNVSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Latamoxef (or moxalactam) is an oxacephem antibiotic usually grouped with the cephalosporins. In oxacephems such as latamoxef, the sulfur atom of the cephalosporin core is replaced with an oxygen atom.

Latamoxef has been associated with prolonged bleeding time, and several cases of coagulopathy, some fatal, were reported during the 1980s.[1][2] Latamoxef is no longer available in the United States. As with other cephalosporins with a methylthiotetrazole side chain, latamoxef causes a disulfiram reaction when mixed with alcohol. Additionally, the methylthiotetrazole side chain inhibits γ-carboxylation of glutamic acid; this can interfere with the actions of vitamin K.[citation needed]

It has been described as a third-generation cephalosporin.[3]

  1. ^ Weitekamp MR, Aber RC (January 1983). "Prolonged bleeding times and bleeding diathesis associated with moxalactam administration". JAMA. 249 (1): 69–71. doi:10.1001/jama.249.1.69. PMID 6217353.
  2. ^ Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M (November 1986). "Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients". Archives of Internal Medicine. 146 (11): 2159–2164. doi:10.1001/archinte.146.11.2159. PMID 3778044.
  3. ^ Salem RR, McIndoe A, Matkin JA, Lidou AC, Clarke A, Wood CB (June 1987). "The hematologic effects of latamoxef sodium when used as a prophylaxis during surgical treatment". Surgery, Gynecology & Obstetrics. 164 (6): 525–529. PMID 3296254.